How to Manage Freelance Employees in 2021

73% of brand marketers expect to rely more on freelance ’employees‘ over the next 2 years (Skyword research). It’s not surprising many companies are looking at ways to ensure the best freelance talent is available to them, as well as ensuring that talent wants to stay. 

Hiring freelance talent, however, is different from hiring employees. Primarily with managers needing to learn how to successfully navigate the differences between managing their employed staff, independent contractors, and freelancers. With employed being full-time staff, contractors being full-time with a limited period of employment, and freelancers being short-term or project-based hires. 

All vital employees require management, but with special considerations depending on their role. This management often involves flexible remote team communication techniques, rolling out the right tools for freelancers, creating a flexible work culture, as well as ensuring the contracting and freelance job force is engaged and content. 

This article goes through the major areas of concern when managing a remote team of freelance employees, as well as overall effective team management. Essentially the ultimate guide to taking full advantage of the flexible work culture!

A Few Points to Kick Off With

When hiring freelance employees, it’s important to remember although they are not long-term members of your team, they still need to feel engaged in your team and company for however long they are working with you. A great leader can work with a team of freelancers to make them feel appreciated from day one whilst also ensuring everyone knows where they stand in the business and management structure. To do this, managers should be regularly checking in with their ongoing project, time-zone impact, and their overall commitment to any project. 

Also, before starting a new freelancer, it’s good to know what you’re both looking to get out of the working relationship. This can be especially helpful when engaging the new team member in discussions about the upcoming work and ensuring it matches well with your freelancer’s upcoming schedules. 

Top tip: When deciding on deadlines, always put your freelancer deadline a few days before your deadline. This ensures any issues can be quickly resolved if needed without delay to the project.

What are the benefits of building relationships with freelancers? 

One might say building a relationship with a new freelance employee is the most important part of it all. For one-off short projects, the relationship may be only skin deep but if you’re looking to work with a contractor long-term, building a solid relationship makes communicating and working with that temporary team member much easier. 

Beyond the transactional, leaders can reap the best of their freelancers by getting to know them better. Questions about family and personal life are great, diving into their purpose and what they’re looking to achieve with their lives. At Work for Impact, what powers us and our purpose is the driving force behind our connections between employers and freelancers. The benefit of this is that being able to center our working relationships around this reminds all involved of the bigger impact and goal, ultimately keeping the team closer together. 

“… When working with people that gets activism. I find there are fewer questions back and forth because they are already there mentally with what you want to accomplish, and they are just trying to apply their skill set to that issue.”

Raymond Laracuenta /CEO and Founder of Oblivion.io Software, makers of WeAct

It can also be helpful to know what drives your freelance employees creatively. Especially when helping them feel more part of your overall creative team. You can ask them questions such as ‘Why does this job appeal to you?’ ‘What are they looking to get from the assignment?’ Or ‘What lights them up at work?’

These opening inquiries can also open the door for new work opportunities, as a freelancer may be able, and keen, to pick up other projects in your pipeline, which otherwise would be left incomplete. A great benefit for any manager looking to increase their output. 

Top Tip: Where possible, include your freelancers in company updates, add them to water-cooler chat groups, and invite them to the team lunches. Make them feel like one of the team!

Building trust with a freelance worker? 

Trust is often easily established through clear communication on both sides, as well as providing support throughout the project and reasonable deadlines. With new digital talent, a great way to start can be with paid-for trial runs or small projects. 

If successfully, then a manager can extend the project and/or give more to the freelancer once they’ve proven their expertise and work ethic. Effective freelancers are often happy to start small, as long as they are compensated for their work regularly and without delay. 

For contractors, trust can be established in the hiring process, as often it can be a more extended process than hiring a freelancer for a project. Asking great questions about expertise, even asking for demonstrations, can establish strong trust from the beginning. Also, ensure to follow up with at least one reference via phone or email. 

When onboarding these new team members, provide brand and style guidelines and key company information that will help them connect to your goals and the bigger picture. Essentially your why. By taking this time to establish a sense of connection to your company for the freelancer, you will help strengthen the trust between you. 

Top Tip: Try a 30-minute onboarding call to bring your freelancer up to speed. This can establish a working relationship that lasts for years.

What’s the best way to communicate with your freelance employees? 

Freelancers, and contractors, are workers who value their autonomy. Clear communication is vital to ensuring the work is done correctly, without the need for micro-management. It’s crucial to have flexible communication with freelancers, as they may often be working on multiple projects and cannot respond to your messages instantly. 

To alleviate any time delays or bottlenecks, managers should discuss the most appropriate communication styles, time expectations, and freelancer software for the new team members to use during their time working with you. Platforms such as Work for Impact allow for clear briefings, as well as messaging services. By containing all communications in one place, it lowers the potential for miscommunication. 

You may find a mix of email and project management tools for project briefings, supported by professionals messaging channels such as Slack for longer-term contractors. It can also be helpful to record specific meetings to make them available to watch by team members who couldn’t be present at the time. 

Additionally, although a brief or project outline should be sufficient, establishing a contact method for the inevitable questions that may arise is essential. For example, you may say, “I will respond to questions via email within 48hrs, and provide access to a Slack channel for questions to be answered by the team within 24 hrs.”

Voice messaging has also become more popular. However, managers should exercise caution in utilizing them. Voice conversations can be great for checking in and creating a more personal connection with a freelancer. However, it’s advisable to ensure all briefs and project information are written down in a platform like Work for Impact or email. This avoids misunderstanding about the work required, especially if the freelancer isn’t a native of your language. 

Top Tip: It doesn’t matter which communication channels you use, just as long as both sides know where to check for communications and how regularly.

What’s the best way to define clear expectations with freelance employees?

There are two major ways to define clear expectations with a freelancer or contractor. These are essentially the same but laid out and utilized differently. For short projects, a single briefing form can be used to outline what is required. Below is a sample briefing document one might use to provide the appropriate information to a content freelancer:

Example: Content Brief

  • Title: The title of the piece (not final)
  • Client: Who is the end client, if not you (provide website if appropriate)
  • Deadline: Add deadline for the piece, and any check-in dates, if needed
  • The Aim:  What is the piece about, and what are its goals? Who is it being targeted to? If there is a specific call to action for the piece.
  • Specifications: Word count range, how do you want it formatted, keywords required?, Tone.
  • Submission: Format for submission, sent to who?
  • Resources: Examples of any previous content, Company key messaging, templates, style guide, mage libraries, etc
  • Fee: Agreed price or rate (if appropriate.)

Alternatively, for bigger projects, you may wish to use a task management system. This works well for larger and long-term projects and is an excellent way to manage expectations on both sides. All of the same information is needed by some categories may need multiple entries, hence the need for a more detailed project briefing. 

Top Tip: Additional training may be required for any company-specific software or processes to ensure the freelancer can hit the ground running.

Projects with multiple tasks will need a project management system to overview the job and see the project broken down into smaller parts. This is great for your freelancing team as they can tick items off as they complete and get the information they need quickly and easily without searching or using your time to ask questions. 

You know you’re doing a great job with your communication with a freelancer when they don’t have to ask you where to get information and instead can pose great ideas or challenge you to do things more efficiently!

“Every relation through Work for Impact has run smoothly. Both how the freelancer interacts with my clients directly or with me has been very seamless, I haven’t had to micromanage anyone hired through the platform, and it has given me peace of mind. I have been able to delegate to the level I want for me to focus on growth.”

Marco Bombardi / Polaris Digital, Founder

This kind of detailed project management works especially well when you might have multiple freelancers, contractors, and full-time staff working on the same client or project. 

Top Tip: Before starting a project, assign each task to a freelancer. This gives them a great overview of their own project deadlines across all their projects.

How do you track the work freelancers perform?

Freelancers are looking to live independent and flexible lives. This is why great communication is key. Of course, though, as a manager, you’ll need to know how a project is getting on, so you can update your progress sheets accordingly, as well as your timelines and budget. Setting up KPIs (Keep Performance Indicators) allows freelancers to track how well they’re performing against several criteria.

Tracking time is also commonly used, as it enables employers to pay freelancers correctly for their efforts. Most commonly used is a freelancer time management tool to do this. Platforms like Work for Impact offer time tracking services as part of their offering, allowing employers to easily track progress and output from their freelancers without multiple emails. In the WFI Time Tracking App, for instance, time is automatically added to your freelancer’s worklog for the project they are working on, as well screenshots taken periodically and saved for both parties to view. This helps both sides to see what work is being done.

Managers should clearly define what should be tracked and how when setting up a freelancer to track their time. (From tracking the main project work to reading emails and conversations with the team, plus general admin time.) With longer-term freelancers, more general admin and non-directly related work need to be accounted for. Track correctly from the get-go, and both parties will be satisfied.  

Top Tip: Set up regular check-ins. These can be daily, weekly, or fortnightly, depending on the need for the project and freelancer.

How often should you connect to offer feedback?

Outside of performance reporting, another essential element of managing freelance employees is to provide feedback. Many freelancers and contractors welcome feedback, with the satisfaction of knowing they’ve done a good job or how they can perform better. This is also helpful to deepening the bonds of your working relationship with them because taking the time to give feedback can strongly show you care about their improvement beyond the task you’ve given them. 

Whether it’s a few minutes at the end of each task, a bigger review at the end of the project, or better yet, continuous feedback, all of these micro-feedbacks will ensure any freelancer continues to do the best job possible. It can also help ensure targets are met, and when sadly, the job isn’t working out, they can be let go of the freelancer quickly before too much time and resources are invested. 

This can also be an advantageous opportunity for managers to ask for feedback from freelancers and listen to their ideas. Freelancers are often highly skilled and happy to share their insights, which can be unique as someone looking in from outside the organization.

A few words of praise alongside feedback can go a long way to show you appreciate what they do for you, and if you can thank them publicly to the team, even better. Gift cards and small gestures with personalized notes are a small cost that can create endless loyalty. 

Top Tip: Recognize and reward freelancers who continue to do a great job. Consistent quality work requiring minimal input from you is priceless.

Finally, what are popular payment methods for freelancers?

An important topic to finish our ultimate freelancer management guide, paying your freelance employees is essential to ensure the continued growth of your business. At Work for Impact, payment to freelancers is made easy through the platform, where all transactions between freelancers and employers are made. This is especially beneficial to employers hiring across continents, as all payments are made through the WFI system, and thus, employers don’t need to worry about complex admin work, multiple payment platforms or unforeseen currency charges. 

Top Tip: Make sure to cover freelancers for their time, whether it’s for onboarding calls, time chatting with team members, or even reading up on industry news to complete your brief.

Before You Go

That’s all for our ultimate guide for hiring and managing freelancers remotely. Let us know if you have any top tips for managing freelancers in our WFI community, where you connect with other employers to see what’s on their minds and learn from their experiences.

 If you’re ready to start hiring, you can sign up to Work for Impact today, which will connect you to highly trained and experienced freelancers, as well as provide the support to hire, set up projects, and get the most out of your working relationships. 

Begin today!